Chris Brown’s Legal Problems: a Timeline of Trouble

Chris Brown’s arrest Tuesday (Aug. 30) by the Los Angeles Police Department on suspicion of assault with a deadly weapon is the latest entry in a laundry list of legal problems that have plagued the 27-year-old singer since his 2009 arrest for assaulting former girlfriend Rihanna.

In the last six months alone, Brown has been sued by his former manager Mike G [Michael Guirguis] for allegedly punching him in the face, and by Suge Knight for failing to provide adequate security at a 2014 party where Knight was shot seven times. He also parted ways with indie publicist Nicole Perna of BWR Public Relations. Today’s events may throw a wrench into release plans for Brown’s eighth studio outing, Heartbreak on a Full Moon — the last album in Brown’s contract with RCA, sources say — which the artist announced via an Instagram post in May he subsequently deleted.

These were only the latest in a long trail of legal entanglements for the troubled singer, as the timeline below shows.

Feb. 8, 2009
At 19, Brown punched, choked and bit his then-girlfriend Rihanna, leaving her with visible facial injuries and in need of hospitalization. Brown turned himself in to the police and later plead guilty to one count of felony assault.

March 22, 2011
Good Morning America co-host Robin Roberts asked Brown repeated questions about Rihanna during his visit to the show, after which the artist stormed off set, and threw a chair through his dressing room window.

June 14, 2012
Brown was involved in a brawl with Drake and his entourage at a New York nightclub, in which about eight people were injured due to broken bottles and punches thrown. The fight was reportedly over Rihanna, whom Drake has also dated.

January 2013

Press reports indicated that there were irregularities in the record submitted to the court concerning Brown’s community service work hours ordered performed in the wake of the Rihanna felony case: He seemed to have been credited with community service work when he was actually out of the United States.

Jan. 27, 2013

Brown was involved in an altercation with Frank Ocean over a parking space outside a recording studio in West Hollywood, California. According to police reports, Brown pushed or punched the singer. Ocean did not press charges, though Brown also reportedly threatened to shoot him, and a member of his entourage used a homophobic slur.

March 7, 2013
Brown became hostile with a valet outside a Los Angeles bowling alley, after the parking attendant requested the $10 charge to release the singer’s car.

July 15, 2013
Brown’s probation was revoked for his involvement in an alleged hit-and-run in Los Angeles. The charges were dropped at a hearing the following month after reaching a “civil compromise” with his accuser. 

Oct. 27, 2013
Brown was arrested for felony assault after punching a man outside the W Hotel in Washington D.C. Brown and his bodyguard allegedly punched a man and broke his nose after he had tried to get in a picture with him and two women. Brown was quoted saying, “I’m not into this gay shit, I’m into boxing,” before taking a swing. Brown’s charge was reduced to a misdemeanor and he voluntarily entered a rehab center while awaiting sentencing.

Nov. 10, 2013
Brown was kicked out of the rehab facility — where he had been expected to stay for three months — for “breaking program rules by acting violently.” He had, according to the facility, thrown a rock through his mother’s car window following a family session, in which she said she wanted him to stay in treatment.

Nov. 20, 2013
Brown was sentenced to 90 days at an anger management rehab facility, as well as submitting to drug testing and to take any prescriptions recommended by the facility. 

Dec. 16, 2013
As a result of Brown’s altercation at the W Hotel in Washington D.C. two months prior, the singer’s probation related to his assault on Rihanna in 2009 was revoked again. However, Brown was not ordered to return to jail, as the judge said he was pleased with his progress in rehab.

March 14, 2014

Brown is kicked out of a Malibu, Calif. rehab facility during a court-ordered extended stay following the W Hotel incident. He’s taken into custody for not taking a drug test and touching a female also undergoing treatment, among other infractions.

Sept. 14, 2015

A Colorado woman filed charges for third-degree assault, alleging she was forcibly thrown off the artist’s tour bus for not giving up her cell phone, which was reportedly broken during the fracas.

June 2, 2016

Following a nightclub performance in Las Vegas, Brown was accused of punching a woman in the face for trying to take his picture.

June 23, 2016

Brown’s former manager Mike G filed suit in Superior Court of the State of California, alleging that Brown assaulted him in an unprovoked, “drug-fueled rage” on May 10, 2016. On Instagram, Brown posts, “N—as is getting mad … because I fired them, because they’re stealing money.”

June 27, 2016

Marion “Suge” Knight sued Chris Brown and West Hollywood nightclub 1 Oak for failing to provide adequate security at a 2014 Brown-hosted party during which Knight was shot seven times.

Aug. 30, 2016

After an all-day standoff with police at his home in Tarzana, Calif. and a subsequent search of the residence, Brown was arrested on suspicion of assault with a deadly weapon. A female alleged the singer had pointed a gun at her face in his home earlier that morning. In a three-part Instagram post, Brown declared, “I’m innocent. I’m tired of this shit.” 

He was released from custody after posting $250,000 bail late Tuesday night and his arraignment has been tentatively set for Sept. 20.

This story first appeared on Billboard.com.